Technology investment, capital allocation and board judgment in the age of AI.
The Fiduciary’s Guide to AI is an ongoing body of work on technology investment, capital allocation, board oversight and the governance disciplines required as AI enters the operating model.
The series examines a practical question facing directors and executives: how should organizations make, monitor and revisit consequential technology decisions as the technology, economics and risks continue to change?
THE SERIES
The Investment Is Working. That Doesn't Mean It Still Deserves the Capital.
Why technology investments should be re-underwritten against today's opportunity set, not yesterday's approval case.
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The Buyer Prices What the Board Deferred
How unresolved technology governance becomes M&A diligence risk, remediation cost and ultimately a question of valuation.
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The Board Has Minutes. It Doesn't Have a Decision Record.
Why boards need decision records that preserve the assumptions, evidence, risks and review triggers behind major technology and AI investments.
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The Board Approved a Thesis. It Didn't Schedule the Retest.
Why boards should retest technology investment assumptions as evidence changes rather than relying on a fixed governance calendar.
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The Board Priced the Compute. It Didn't Price the Governance.
Why the true cost of AI includes the controls, oversight, data discipline and operating infrastructure required to use it responsibly at scale.
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Why Every Technology Investment Needs a Stop Rule
Why boards should define in advance the conditions that would trigger reassessment, restructuring or withdrawal of capital from a technology investment.
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Five Questions to Ask Before Your Board Funds Emerging Technology
A practical framework for testing whether a proposed technology investment has a clear strategic case, measurable economics, accountable ownership and defined downside.
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Recent work applying these disciplines to underwriting, post-close execution and sponsor-backed value creation.
Every Add-Back Becomes a 100-Day Question
How execution-dependent EBITDA adjustments become post-close obligations and operating commitments.
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The Assumption Has an Owner. Who Can Change the Plan?
Why value-creation plans need clear decision rights when assumptions begin to slip.
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The Initiative Hasn't Changed. The Clock Has.
How the remaining hold period changes what can be realized, evidenced and priced before exit.
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